The 1989–90 FA Cup was the 109th season of the world's oldest football knockout competition, the Football Association Challenge Cup, or FA Cup for short. The competition started in September 1989 with the Preliminary Round and continued through to the Final Replay in May 1990 in which Manchester United defeated Crystal Palace.
Qualifying rounds Most participating clubs that were not members of the Football League competed in the qualifying rounds to secure one of 28 places available in the first round.
The winners from the fourth qualifying round were Northwich Victoria, Billingham Synthonia, Whitley Bay, Marine, Tow Law Town, Darlington, Congleton Town, Bishop Auckland, Stafford Rangers, Redditch United, Halesowen Town, Kidderminster Harriers, Welling United, Slough Town, Farnborough Town, Dartford, Matlock Town, Barnet, Aylesbury United, Bromsgrove Rovers, Merthyr Tydfil, Dorchester Town, Hayes, Basingstoke Town, Gloucester City, Woking, Yeovil Town and Bath City.
Appearing in the competition proper for the first time were Whitley Bay and Congleton Town. Of the others, Dorchester Town had last featured at this stage in 1981–82, Matlock Town had last done so in 1976-77, Marine had last done so in 1975-76, Redditch United and Basingstoke Town had last done so in 1971-72 and Gloucester City had not done so since 1950-51.
Meanwhile, Darlington matched the achievements of Lincoln City two seasons previously in winning promotion back to the Football League at the first attempt after being relegated to the Football Conference. The Quakers managed to hold off a challenge from Barnet to take the Conference championship, and advanced to the third round of the FA Cup where Fourth Division Cambridge United needed a replay to end their run.
First round proper The 48 teams from the Football League Third and Fourth Divisions entered in this round along with the 28 non-league clubs from the qualifying rounds and Telford United, Macclesfield Town, Kettering Town and Sutton United who were given byes. The first round of games was played over the weekend 17–19 November 1989, with a first round of replays being played on the 21st–22nd. The Bristol Rovers–Reading match went to a second replay, on the 27th. Billingham Synthonia and Tow Law Town, from the Northern League at Step 8 of English football, were the lowest-ranked teams in the round.
Tie noHome teamScoreAway teamDate1Blackpool2–1Bolton Wanderers18 November 19892Darlington (5)6–2Northwich Victoria (5)18 November 19893Dartford (6)1–1Exeter City18 November 1989ReplayExeter City4–1Dartford22 November 19894Bath City (6)2–2Fulham19 November 1989ReplayFulham2–1Bath City22 November 19895Bristol City2–0Barnet (5)18 November 19896Burnley1–1Stockport County18 November 1989ReplayStockport County1–2Burnley22 November 19897Preston North End1–0Tranmere Rovers18 November 19898Sutton United (5)1–1Torquay United18 November 1989ReplayTorquay United4–0Sutton United22 November 19899Marine (6)0–1Rochdale17 November 198910Gillingham0–0Welling United (5)18 November 1989ReplayWelling United1–0Gillingham22 November 198911Macclesfield Town (5)1–1Chester City18 November 1989ReplayChester City3–2Macclesfield Town21 November 198912Crewe Alexandra2–0Congleton Town (7)18 November 198913Lincoln City1–0Billingham Synthonia (8)18 November 198914Stafford Rangers (5)2–3Halifax Town18 November 198915Scarborough0–1Whitley Bay (7)18 November 198916Shrewsbury Town2–3Chesterfield18 November 198917Doncaster Rovers1–0Notts County18 November 198918Bishop Auckland (6)2–0Tow Law Town (8)18 November 198919Kidderminster Harriers (5)2–3Swansea City18 November 198920Aylesbury United (6)1–0Southend United18 November 198921Brentford0–1Colchester United18 November 198922Bristol Rovers1–1Reading18 November 1989ReplayReading1–1Bristol Rovers21 November 1989ReplayBristol Rovers0–1Reading27 November 198923Maidstone United2–1Yeovil Town (5)19 November 198924Carlisle United3–0Wrexham18 November 198925Scunthorpe United4–1Matlock Town (6)18 November 198926Cardiff City1–0Halesowen Town (7)18 November 198927York City1–2Grimsby Town18 November 198928Kettering Town (5)0–1Northampton Town18 November 198929Rotherham United0–0Bury18 November 1989ReplayBury1–2Rotherham United21 November 198930Aldershot0–1Cambridge United17 November 198931Gloucester City (6)1–0Dorchester Town (6)18 November 198932Wigan Athletic2–0Mansfield Town19 November 198933Peterborough United1–1Hayes (6)18 November 1989ReplayHayes0–1Peterborough United21 November 198934Leyton Orient0–1Birmingham City18 November 198935Basingstoke Town (6)3–0Bromsgrove Rovers (6)18 November 198936Slough Town (6)1–2Woking (7)18 November 198937Telford United (5)0–3Walsall18 November 198938Redditch United (7)1–3Merthyr Tydfil (5)18 November 198939Farnborough Town (5)0–1Hereford United18 November 198940Hartlepool United0–2Huddersfield Town18 November 1989
Second round proper
The second round of games was played on 9 December 1989, with the first round of replays being played on the 12th–13th. Two games went to second replays and one of these went to a third replay. The round featured two teams from Step 7 of the English football system: Whitley Bay from the Northern Premier League First Division, and Woking from the Isthmian League First Division.
Tie noHome teamScoreAway teamDate1Blackpool3–0Chester City9 December 19892Chesterfield0–2Huddersfield Town9 December 19893Darlington (5)3–0Halifax Town9 December 19894Bristol City2–1Fulham9 December 19895Rochdale3–0Lincoln City9 December 19896Reading0–0Welling United (5)9 December 1989ReplayWelling United1–1Reading13 December 1989ReplayReading0–0Welling United19 December 1989ReplayWelling United1–2Reading22 December 19897Walsall1–0Rotherham United9 December 19898Grimsby Town1–0Doncaster Rovers9 December 19899Crewe Alexandra1–1Bishop Auckland (6)9 December 1989ReplayBishop Auckland0–2Crewe Alexandra13 December 198910Maidstone United1–1Exeter City9 December 1989ReplayExeter City3–2Maidstone United13 December 198911Northampton Town0–0Aylesbury United (6)9 December 1989ReplayAylesbury United0–1Northampton Town13 December 198912Whitley Bay (7)2–0Preston North End9 December 198913Scunthorpe United2–2Burnley9 December 1989ReplayBurnley1–1Scunthorpe United12 December 1989ReplayBurnley5–0Scunthorpe United18 December 198914Cardiff City2–2Gloucester City (6)9 December 1989ReplayGloucester City0–1Cardiff City12 December 198915Hereford United3–2Merthyr Tydfil (5)9 December 198916Wigan Athletic2–0Carlisle United9 December 198917Colchester United0–2Birmingham City9 December 198918Basingstoke Town (6)2–3Torquay United9 December 198919Cambridge United3–1Woking (7)9 December 198920Swansea City3–1Peterborough United9 December 1989
Third round proper
Teams from the Football League First and Second Division entered in this round. The third round of games in the FA Cup was played over the weekend 6–7 January 1990, with the first set of replays being played on the 9th–10th. Two games went to second replays, which were completed during the following week. Whitley Bay (Step 7) was again the lowest-ranked team in the draw, and they and Darlington were the last non-league clubs left in the competition.
Tie noHome teamScoreAway teamDate1Blackpool (3)1–0Burnley (4)6 January 19902Bristol City (3)2–1Swindon Town (2)6 January 19903Rochdale (4)1–0Whitley Bay (7)6 January 19904Watford (2)2–0Wigan Athletic (3)6 January 19905Reading (3)2–1Sunderland (2)6 January 19906Leicester City (2)1–2Barnsley (2)6 January 19907Nottingham Forest (1)0–1Manchester United (1)7 January 19908Blackburn Rovers (2)2–2Aston Villa (1)6 January 1990ReplayAston Villa3–1Blackburn Rovers10 January 19909Wolverhampton Wanderers (2)1–2Sheffield Wednesday (1)6 January 199010Middlesbrough (2)0–0Everton (1)6 January 1990ReplayEverton1–1Middlesbrough10 January 1990ReplayEverton1–0Middlesbrough17 January 199011West Bromwich Albion (2)2–0Wimbledon (1)6 January 199012Sheffield United (2)2–0AFC Bournemouth (2)6 January 199013Tottenham Hotspur (1)1–3Southampton (1)6 January 199014Manchester City (1)0–0Millwall (1)6 January 1990ReplayMillwall1–1Manchester City9 January 1990ReplayMillwall3–1Manchester City15 January 199015Northampton Town (3)1–0Coventry City (1)6 January 199016Brighton & Hove Albion (2)4–1Luton Town (1)6 January 199017Plymouth Argyle (2)0–1Oxford United (2)6 January 199018Hull City (2)0–1Newcastle United (2)6 January 199019Crystal Palace (1)2–1Portsmouth (2)6 January 199020Chelsea (1)1–1Crewe Alexandra (3)6 January 1990ReplayCrewe Alexandra0–2Chelsea10 January 199021Exeter City (4)1–1Norwich City (1)6 January 1990ReplayNorwich City2–0Exeter City10 January 199022Huddersfield Town (3)3–1Grimsby Town (4)6 January 199023Cardiff City (3)0–0Queens Park Rangers (1)6 January 1990ReplayQueens Park Rangers2–0Cardiff City10 January 199024Port Vale (2)1–1Derby County (1)7 January 1990ReplayDerby County2–3Port Vale10 January 199025Charlton Athletic (1)1–1Bradford City (2)7 January 1990ReplayBradford City0–3Charlton Athletic10 January 199026Leeds United (2)0–1Ipswich Town (2)6 January 199027Torquay United (4)1–0West Ham United (2)6 January 199028Hereford United (4)2–1Walsall (3)6 January 199029Stoke City (2)0–1Arsenal (1)6 January 199030Birmingham City (3)1–1Oldham Athletic (2)6 January 1990ReplayOldham Athletic1–0Birmingham City10 January 199031Cambridge United (4)0–0Darlington (5)6 January 1990ReplayDarlington1–3Cambridge United9 January 199032Swansea City (3)0–0Liverpool (1)6 January 1990ReplayLiverpool8–0Swansea City9 January 1990
Fourth round proper
The fourth round of games was played over the weekend 27–28 January 1990, with replays being played on the 30th–31st. Fourth Division sides Rochdale, Torquay United, Hereford United and Cambridge United were the lowest-ranked teams in the draw.
Tie noHome teamScoreAway teamDate1Blackpool1–0Torquay United27 January 19902Bristol City3–1Chelsea27 January 19903Rochdale3–0Northampton Town27 January 19904Southampton1–0Oxford United27 January 19905Reading3–3Newcastle United27 January 1990ReplayNewcastle United4–1Reading31 January 19906Aston Villa6–0Port Vale27 January 19907Sheffield Wednesday1–2Everton28 January 19908West Bromwich Albion1–0Charlton Athletic27 January 19909Sheffield United1–1Watford27 January 1990ReplayWatford1–2Sheffield United30 January 199010Barnsley2–0Ipswich Town27 January 199011Norwich City0–0Liverpool28 January 1990ReplayLiverpool3–1Norwich City31 January 199012Millwall1–1Cambridge United27 January 1990ReplayCambridge United1–0Millwall30 January 199013Oldham Athletic2–1Brighton & Hove Albion27 January 199014Crystal Palace4–0Huddersfield Town27 January 199015Arsenal0–0Queens Park Rangers27 January 1990ReplayQueens Park Rangers2–0Arsenal31 January 199016Hereford United0–1Manchester United28 January 1990
Fifth round proper
The fifth set of games was played over the weekend 17–18 February 1990, with a first round of replays being played on the 21st. Each of these finished in a draw, meaning a second round of replays had to be completed. Rochdale and Cambridge United were again the lowest-ranked teams in the round.
Tie noHome teamScoreAway teamDate1Blackpool2–2Queens Park Rangers18 February 1990ReplayQueens Park Rangers0–0Blackpool21 February 1990ReplayQueens Park Rangers3–0Blackpool26 February 19902Bristol City0–0Cambridge United17 February 1990ReplayCambridge United1–1Bristol City21 February 1990ReplayCambridge United5–1Bristol City27 February 19903Liverpool3–0Southampton17 February 19904West Bromwich Albion0–2Aston Villa17 February 19905Sheffield United2–2Barnsley18 February 1990ReplayBarnsley0–0Sheffield United21 February 1990ReplayBarnsley0–1Sheffield United5 March 19906Newcastle United2–3Manchester United18 February 19907Oldham Athletic2–2Everton17 February 1990ReplayEverton1–1Oldham Athletic21 February 1990ReplayOldham Athletic2–1Everton10 March 19908Crystal Palace1–0Rochdale17 February 1990
Sixth round proper